Acetic Acid → HCID 67418881, compound

HRID 245141Notes

Reaction equation

HRID 245141 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[NH:18]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.[OH-].[Na+]>[OH:23][C@H:20]1[CH2:21][CH2:22][N:18]([CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]2)[CH2:19]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 2733874(3S)-pyrrolidin-3-olHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67418881HCID 67418881, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of phenylmethyl 4-oxo-1-piperidinecarboxylate (1 g, 4.29 mmol) and (3S)-3-pyrrolidinol (0.411 g, 4.72 mmol) in 1,2-dichloroethane (14.29 mL) was treated at room temperature under air with sodium triacetoxyborohydride (1.363 g, 6.43 mmol) and glacial acetic acid (0.245 mL, 4.29 mmol). After 16 h, the mixture was diluted with 1N NaOH (75 mL) and extracted with methylene chloride (3×75 mL). The combined organic extracts were washed with brine (1×75 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford phenylmethyl 4-[(3S)-3-hydroxy-1-pyrrolidinyl]-1-piperidinecarboxylate (1.35 g, 98% yield). This material was used in the next step without further purification. MS (m/z) 305.0 (M+H+).

Workup

  1. extractionextracted with methylene chloride (3×75 mL)
  2. washThe combined organic extracts were washed with brine (1×75 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-518ae32c2fa74314b5c9577482f43b8a
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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